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The quest for excellence requires the taking of risks, and the Upper School faculty fosters an atmosphere in which students feel comfortable in seeking different intellectual avenues. The continued balance between academic vigor and a nurturing learning environment gives students the skills necessary to meet new experiences. Core academic subjects include English, mathematics, history, science, athletics, and fine arts. Latin is required in Grades Five and Six, while a choice of Spanish or Latin is offered in Grades Seven and Eight. Skills acquisition remains a goal at all grade levels, but organizational and problem-solving strategies are special emphases of Upper School.

One unique feature of the Gulf Stream School curriculum is our Winterim program. Every other year, Seventh and Eighth Grade students have the opportunity to spend a week in Montreal and Quebec City. In the weeks leading up to the trip they learn about the culture and history of Canada. During their visit, they combine historically and culturally educational activities with fun activities such as dog sledding, snow shoeing, and sledding. In the year between the Canada trips, Seventh and Eighth Graders may elect to participate in a two-day trip to Crystal River, Florida where they swim with the manatees. Students who remain at school during the optional trips are presented with a variety of fun and educational activities. Recent examples include spending a day with a local chef, picking vegetables for his restaurant, and preparing a meal; spending a morning with an operating room nurse learning how to scrub and prepare an operating room; and visiting the studio of a world-renowned artist, both to learn about his work and to create projects of their own.

With school e-mail accounts beginning in Grade Five and their own tablet computers, beginning in Grade Six, students incorporate technology into core academic subjects. Unique challenges such as the publication of our School literary magazine, The Nautilus, by the Seventh Grade and the School yearbook, The Mariner by the Eighth Grade, as well as the traditional Eighth Grade term papers and speeches to the Upper School community, help students apply skills they have learned in the classroom during their Gulf Stream careers.

All Upper School students and their parents sign an academic honor code and a technology code of conduct in order to reinforce a high level of personal integrity as well as a cooperative and constructive environment for learning.